Sodium Carbonate → Methyl (S)-3-amino-3-phenylpropanoate

HRID 2102877Notes

Reaction equation

HRID 2102877 reaction equation
[NH2:1][C@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][C:7](C)(C)C)=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>Cl>[NH2:1][C@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 70210931,1-Dimethylethyl (betaS)-beta-aminobenzenepropanoate

Product 1

HCID 788099Methyl (S)-3-amino-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (3S)-3-amino-3-phenylpropanoate (5.04 g, 22.9 mmol) in 2.25M methanolic hydrogen chloride (100 ml) was heated under reflux for 2½ hours. The mixture was cooled to room temperature, basified with saturated aqueous sodium carbonate solution to pH 8 and the phases separated. The aqueous layer was extracted with dichloromethane (4×). The combined organic solutions were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound, 3.97 g;

Workup

  1. temperatureunder reflux for 2½ hours
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with dichloromethane (4×)
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-21d888c986e842f3afed0b07c2bc88c9
Source dataset
uspto-grants-2009_08
Patent number
US07576097B2

Reaction notes

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